Webthe journey from milwaukee to chicago can take as little as 1 hour 25 minutes and starts from as little as $18. 49. The earliest bus leaves at 3:20 am and the last bus leaves at. Webbuses run every two hours between milwaukee and chicago o'hare airport (ord). The service departs milwaukee at 18:40 in the evening, which arrives into chicago o'hare. Webamtrak operates a train from milwaukee to chicago union station every 4 hours. Alternatively, greyhound usa operates a. Webamtrak operates a train from milwaukee to chicago union station every 4 hours. Alternatively, greyhound usa operates a.
